Culper Ring

British Army occupation of New York City

Under pressure from American colonial forces, the British Army under General William Howe evacuated Boston, Massachusetts on March 17, 1776 and sailed for Halifax, Nova Scotia to reorganize. Before Howe's forces had completed their departure, American General George Washington had begun to move his troops to New York City, where most had arrived by mid-April to begin preparing defenses. Washington correctly suspected that Howe would return to New York City to make it the British base of operations.

General Howe's troop ships began to arrive at New York Harbor on June 28, 1776. On July 3, 1776, Howe's men began to land at undefended Staten Island. General Howe's brother Vice Admiral Richard Howe arrived the following week to take charge of the British naval force. British and Hessian soldiers continued to arrive until August 12, 1776. Washington did not have a spy network in New York that he could count on for intelligence, as he could from the many Patriots who had previously organized to spy on the British Army at Boston. On the other hand, the British could depend on the many Loyalists at New York City for intelligence. So Washington divided his smaller force in order to defend several possible locations on Long Island and Manhattan Island, where the British might attack.

When General Howe had all of his forces in place, his initial moves did not alert Washington to the full danger that the Continental Army faced because Washington's intelligence operatives seriously underestimated British troop strength. On August 22, 1776, British Army troops from Staten Island landed on Long Island to begin the New York and New Jersey campaign to drive the Continental Army from New York City.

First, on August 27, 1776, the British overwhelmed the American defenders at the Battle of Long Island, forcing the Americans back to their fortifications on Brooklyn Heights. On August 30, 1776, Washington's troops quietly withdrew from Long Island to Manhattan before the British could attack the outnumbered and demoralized Americans. On September 15, General Howe attacked the Continental Army force stationed at New York City, then located only on lower Manhattan. They landed at Kip's Bay and drove the Americans out of the city, capturing all of the cannon that they had there. The Americans were victorious the following day at the Battle of Harlem Heights on September 16, but Howe forced the Continental Army to abandon Manhattan entirely through a series of maneuvers and engagements, most significantly the Battle of Fort Washington, where the British took almost 3,000 prisoners on November 16.

By early December, the Americans had been forced to withdraw across New Jersey to Pennsylvania. The British controlled New York City and made it their military headquarters and base of operations until the war ended in 1783.

According to some sources, Washington's crucial successful attack on the Hessian garrison at Trenton, New Jersey on December 26 was greatly aided by an American spy of Irish descent named John Honeyman, who provided information on the Hessian camp and the Hessians' planned Christmas celebration. Honeyman also gave the Hessians false intelligence about the condition of the Continental Army. Alexander Rose debunks the Honeyman story, however, in an article for the CIA's Studies in Intelligence Journal, tracing it to his daughter and grandson. The story had been widely accepted, but Rose notes that David McCullough took no note of it in his book 1776. He also quotes Historian David Hackett Fischer in Washington's Crossing: "[The story] might possibly be true but in the judgement of this historian, the legend of Honeyman is unsupported by evidence. No use of it is made here."

Early American intelligence operations in New York City

Before Howe moved from Staten Island, Washington received information of varying utility from individual agents, such as Lawrence Mascoll, who obtained some intelligence on Staten Island before August 23. After evacuating his troops from Brooklyn Heights, Washington asked Brigadier General William Heath and New York militia general George Clinton to set up "a channel of information" on Long Island. (Clinton was soon to become Governor of New York and later was Vice President of the United States.) Washington did not yet try to establish permanent agents behind enemy lines. His next agent was the untrained and easily recognized Captain Nathan Hale, who was captured during his effort to obtain intelligence in New York City by the cunning and ruthless Loyalist ranger Lieutenant Colonel Robert Rogers, and summarily executed by the British on September 22, 1776.

By January 1777, Washington thought that civilians would attract less attention as spies and that they must recruit other agents to gather intelligence. He asked William Duer, a member of the New York Committee for Detecting and Defeating Conspiracies of the New York Provincial Congress, to recommend someone to be the agent. Duer recommended colleague Nathaniel Sackett. Washington appointed Captain Benjamin Tallmadge, a classmate and friend of Nathan Hale, to be Sackett's contact with the army.

Tallmadge was promoted to major on April 7, 1777. His regiment was called from Connecticut to join the main body of the Continental Army and he had little time to devote to intelligence work. Sackett had developed some advancements and new methods for spying, such as keeping an agent in enemy territory and finding a means of regular communication, which he detailed in a letter to Washington on April 7, the date of Tallmadge's promotion. Sackett also recruited a few agents, whose identities remain unknown. He discovered that the British were building flat-bottomed boats to use in a campaign against Philadelphia. Sackett had not produced enough correct intelligence fast enough for Washington, however, and he was soon paid and dismissed. Early in 1777, American Colonel Elias Dayton set up a spy network on Staten Island to work in parallel with established American intelligence agent John Mersereau.

British Army occupation of and withdrawal from Philadelphia

Sackett was correct about Howe's intention to move against Philadelphia. Howe moved his force by water to Head of Elk, Maryland on Chesapeake Bay because he believed that the American defenses on the Delaware River were too strong to attack. Washington failed to stop the British at the Battle of Brandywine on September 11, 1777 and the British took Philadelphia on September 26. The focus of intelligence gathering switched to Philadelphia, and Washington assigned Major John Clark, who had returned to the army from successfully spying on Long Island but had been severely wounded in a skirmish before the Battle of Brandywine. Clark set up a successful network of spies but his unhealed wound and constant exertions wore him out and he had to retire to a desk job.

By the late Spring of 1778, the British found Philadelphia too difficult to supply and too vulnerable to attack. Their new commander-in-chief General Sir Henry Clinton was ordered to leave Philadelphia and defend New York City. France had allied with the Americans, which increased the possibility of an attack on the British at New York. Clinton began to evacuate Philadelphia on June 10, 1778. The Continental Army attacked the British during their return to New York at the Battle of Monmouth on June 28, hastening the British movement. Clinton's forces retreated to Sandy Hook, New Jersey and, from there, they took ships for New York City, which they had already occupied for almost two years.

Initial formation

The focus of intelligence gathering returned to New York, where Washington lacked a spy network. On August 7, 1778, Washington received a letter from Lieutenant Caleb Brewster at Norwalk, Connecticut with an offer to report on the enemy, to which Washington cautiously agreed and replied with advice. Brewster sent his first report on August 27, including the condition of British warships after a storm and some battles with French warships at the beginning of the Battle of Rhode Island. Brewster also reported that several regiments of British troops were boarding ships to take them to Newport, Rhode Island.

Washington assigned General Charles Scott to handle Brewster and find additional agents. He also asked Major Benjamin Tallmadge to assist Scott. Scott had many other duties and he found intelligence work uninteresting, so Tallmadge did most of the intelligence work. Washington soon directly asked Tallmadge to recruit people who could be trusted to collect intelligence in New York City.

Tallmadge recommended Abraham Woodhull of Setauket in Suffolk County on Long Island as a contact for Brewster. Woodhull was a childhood friend of both Brewster and Tallmadge. A few months earlier, Woodhull had been taken prisoner by an American ship and charged with illegal trading, of which he was in fact guilty. He was held in Connecticut until Tallmadge quietly talked with Governor Jonathan Trumbull, who released Woodhull. Before Woodhull left Connecticut, Tallmadge spoke with him about joining Washington's secret service. In a dinner with Washington and Scott on August 25, Tallmadge convinced Washington that Woodhull was trustworthy. At that dinner, the officers devised the alias "Samuel Culper" for Woodhull, with Washington suggesting Culper as a variation of Culpeper County, Virginia where he had worked as a surveyor in his youth.

Tallmadge was not getting along well with the difficult Scott, and their approaches to spying differed. Scott wished to continue using single-mission agents to sneak in and out of enemy lines, while Tallmadge favored embedding spies in enemy territory and establishing a secure line of communication back to base. Scott lost three of five agents sent to spy on the British in New York City in early September, and Washington decided that Tallmadge's method should be used. He was communicating directly with Tallmadge as early as October 22 about setting up a network with Woodhull and Brewster. On October 29, Scott resigned as chief of intelligence, and Washington assigned Tallmadge to lead the intelligence network.

Early operations

At first, Woodhull would go to New York City every few weeks to gather intelligence. His married sister Mary Underhill lived there, giving him a reason to visit. On October 31, he was questioned at a British checkpoint, increasing his anxiety about the dangerous mission. Nonetheless, he returned to Setauket with valuable information about the British supply fleet. On November 23, 1778, Woodhull provided a precise report on the identity of British units and the numbers of troops and dispositions in New York City, proving his worth as a spy. Woodhull soon recruited his brother-in-law Amos Underhill to gather intelligence, who ran a boarding house in the city with his wife Mary, but Underhill's reports were often too vague to be of much value.

At first, Woodhull had to return to Setauket to pass messages to Caleb Brewster, which he would take to Tallmadge, or to receive messages from Tallmadge via Brewster. By December 1778, Tallmadge set up couriers, at first Jonas Hawkins, then in the early summer mainly Austin Roe, who would take messages the 55 miles (89 km) between New York and Setauket to pass them to Brewster. The courier's task was to get the letters to Brewster who would pick up messages at one of six secluded coves near Setauket and, with his rotating whaleboat crews, take them across the Sound to Tallmadge at Fairfield, Connecticut. Tallmadge would then take them to Washington's headquarters. This time-consuming task was replaced in January 1779 by the assignment of express riders to take the messages from Tallmadge to Washington.

Local tradition claims that Anna Strong, a resident of Setauket and a friend and neighbor of Abraham Woodhull, helped pass along messages from the spy ring by posting pre-arranged signals to indicate when one of the spies was ready to submit intelligence. If Strong hung a black petticoat on her clothesline, it meant that Brewster had arrived in town in his whaleboat. Next to that, she would hang a quantity of white handkerchiefs. The specific number of handkerchiefs indicated one of six hiding places where Brewster might be located. Woodhull used Strong's signals to meet Brewster or to drop messages at one of the meeting places. Historian Richard Welch writes that the tradition of the clothesline signal is unverifiable, but it is known that the British had a woman at Setauket under suspicion for disloyal activities who fits Anna's profile.

Brewster occasionally would add his own report to the Culper messages. In a January 1779 report received by Washington in early February, Brewster sent some information about naval matters and boat building at New York City and warned that local Loyalists were outfitting privateers for operations on Long Island Sound.

Brewster's message about naval matters was with a message from Woodhull which precisely described the British regiments and commanders at the northern tip of Manhattan, totaling about 8,500 men. Woodhull also reported on British boat-building, confirming Brewster's report. Tallmadge and Washington thought that the boats might be planned transport for an attack by water, possibly against Connecticut, from New York Royal Governor and Major General (of Provincials) William Tryon, who already had conducted a raid during the winter.

Through Spring 1779, Woodhull became increasingly anxious about being discovered and did little in May and June. John Wolsey was a Long Island privateer who was captured by the British. In order to secure parole, he told British officers on June 5 that he had heard that Abraham Woodhull was up to something dubious. While Woodhull was away in New York City, Colonel John Graves Simcoe, commander of the Queen's Rangers, came to Setauket to look for him. Not finding Woodhull at home, Simcoe's men attacked and beat Woodhull's father Judge Richard Woodhull. Abraham Woodhull escaped arrest because Loyalist militia officer Colonel Benjamin Floyd vouched for him. (Floyd had married his distant relative Ruth Woodhull, a sister or cousin of New York militia Brigadier General Nathaniel Woodhull.)

In late June, Washington sent a letter to Tallmadge in which he identified George Higday as a possible operative to relieve Woodhull in New York City. The British had intercepted a June 13 letter from Washington referring to C_____s, "a liquid," and Tallmadge. On July 2, British cavalry under the command of Colonel Banastre Tarleton attacked Tallmadge's camp and captured his horse and some papers, including the letter mentioning Higday. They were trying to capture Tallmadge himself because they knew that he was head of Washington's intelligence operation. The second letter, captured from Tallmadge, confirmed that an agent C______ was operating in New York City and that Tallmadge was the chief intelligence officer for Washington. Higday escaped execution but was of no use as a spy to Washington or to Clinton, who tried to recruit him as a double agent.

Woodhull reported that, after the June incident at Setauket, he could not continue to operate in New York City because he was still under suspicion, but he had a new agent for New York City lined up and would go to New York to finalize arrangements with him.

Expansion of the Ring

In June 1779, Woodhull engaged Robert Townsend to gather intelligence in New York City, using the alias "Samuel Culper, Jr." Townsend was engaged in business there, and his presence was expected to arouse less suspicion than Woodhull's visits would. He also had access to British officers through several channels, including his own tailoring business. He wrote a society column in a Loyalist newspaper, and he owned an interest in a coffeehouse with Loyalist newspaper owner James Rivington, who also was a secret member of the Ring.

After Townsend began his intelligence activities in New York City, Woodhull operated almost exclusively from Setauket. A revised communications network was then established, in which Townsend would pass intelligence to a courier—at first Hawkins, then Hawkins and Roe, and exclusively Roe after September 1779. The courier would take it to Setauket and pass it to Woodhull, usually via dead drop in a box hidden in a field which Roe rented from Woodhull. Woodhull would evaluate and comment on it and pass it to Brewster, who would take it across Long Island Sound, occasionally adding an intelligence note of his own, and pass it to Tallmadge. Tallmadge would usually add a cover letter with comments.

As noted before, tradition holds and many sources state that Anna Strong signalled Brewster that a message was ready with a black petticoat on her clothesline in Setauket, which was easily visible by Brewster from a boat in the Sound and by Woodhull from his nearby farm. Tallmadge sent the messages, or received messages from Washington by a relay of dragoons acting as couriers.

Hawkins at first was bold but became increasingly anxious about British patrols. His role was reduced between April (when Woodhull identified both Hawkins and Roe as couriers for the Ring) and July (when Tallmadge gave Roe a code number in his code directory, but not Hawkins).

Woodhull wrote in a coded message on August 15 that Hawkins had to destroy a letter from Culper, Jr. or be captured. In his August 15 message, Woodhull wrote that Hawkins insisted that his next meeting with Townsend be in an out of the way location. Townsend did not like taking the additional risk and was beginning to doubt Hawkins's reliability and to regret the destroyed messages. Finally in September 1779, Hawkins stopped his courier services for the Ring, as Townsend refused to deal with him any longer. Woodhull acted as courier on September 11 so that he could explain to Townsend the loss of the earlier letters. Austin Roe then became the sole permanent courier for the Ring.

Secrecy

Secrecy was so strict that Washington did not know the identity of all the operatives. Townsend was recruited by Woodhull and was especially insistent that his identity not be revealed, although Austin Roe and Jonas Hawkins needed to know him. (Roe was the Ring's main courier between New York City and Setauket, and Hawkins was his predecessor before September 1779 and occasional backup thereafter.)

Among the techniques that the Ring used to relay messages were coded messages published in newspapers and invisible ink, called a sympathetic stain, to write between the lines of what appeared to be typical letters.

Washington made sure that the Culper Ring spies had more support and operated in greater secrecy than previous Continental spies, perhaps with Nathan Hale in mind. Through Tallmadge, he provided them with codes, dead drops, and aliases. Tallmadge, Woodhull, and Townsend were given code names. They were also given code numbers, along with Washington, Brewster, Roe, and Rivington. George Washington's code number was 711.

Some sources note a female member of the ring, known only as Agent 355, while others believe that this code number referred to Anna Strong or was simply a misunderstanding of a cryptic reference in one of Abraham Woodhull's letters.

Hercules Mulligan and Cato

Hercules Mulligan was recruited to spy for the Continental Army in New York City by Alexander Hamilton. He was born in 1740, was a friend of Townsend's father, and was an active member of the Sons of Liberty. He had taken in Alexander Hamilton when he arrived in New York as an orphan in 1773 to attend King's College (later Columbia University), and had helped Hamilton obtain a commission in the army. He was married to Elizabeth Sanders, daughter of a Royal Navy admiral, and he also had a fashionable clothing business near Robert Townsend's establishment—and these things gave him access to officers who would talk to him about military matters.

Alexander Rose describes Mulligan as a "subagent of the Culper Ring." He wrote that Mulligan began his activities within six weeks of the date when Townsend sent his first Culper letter. Mulligan, however, began his activities in late 1776 or early 1777, well before formation of the Culper Ring. Historian Stephen Knott says that Mulligan co-operated with the Culper Ring, but mostly operated as a lone agent. Alexander Rose states that Mulligan gave Townsend information, which Townsend added to his reports.

Mulligan's African-American slave Cato was his "faithful accomplice" in his intelligence activities, which began no later than April 1777, over a year before the formation of the Culper Ring. In January 1779, Cato delivered a message from Mulligan to George Washington's aide Alexander Hamilton that the British planned to kidnap or kill American leaders, including Washington and New Jersey Governor William Livingston. Mulligan had received the information from his brother Hugh, who was with Kortright and Company, a contractor for the British Army. Washington and Livingston took appropriate precautions.

The British arrested Mulligan on suspicion of espionage after Benedict Arnold defected in New York. Townsend ceased his activities for a time for fear that he, also, would be discovered. Woodhull passed on the information concerning Townsend's dejection and concern over the arrest of "one that hath been ever serviceable to this correspondence." Arnold did not have any hard evidence against Mulligan, so he was released, but he may have spent as many as five months in prison, until February 1781. Author Harry Thayer Mahoney wrote that it was a "failure of British counterintelligence" when the British failed to lock up Mulligan except for a short time.

Mulligan continued to pick up intelligence after his release. He discovered that the British planned to ambush Washington while he was on his way to a meeting with Rochambeau on March 5, 1781. Mulligan and Cato remained under suspicion and could not communicate directly with Washington's headquarters, so Mulligan gave the information to Townsend, who sent it to Washington via the Culper Ring network. The message arrived in time for Washington to avoid the trap and travel to the meeting by another route.

Other persons identified as informants

The members of the ring gathered information from a variety of sources, including persons other than unwitting British officers. Some of those informants or associates included Joseph Lawrence, a Long Island resident; Captain Nathan Woodhull, Woodhull's uncle who served as a Loyalist militia officer but provided information to Abraham Woodhull; Nathaniel Ruggles, a schoolmaster and physician born in 1713; Joshua Davis, a Brewster deputy and occasional substitute; George Smith, a whaleboat man who filled in for Brewster near the end of the war; and William T. Robinson, a merchant.

Alexander Rose wrote that John Cork was a code name for an unidentified informant. Harry Thayer Mahoney wrote that John Corke of Groton, New York posed as a Tory and could travel back and forth to New York City because he was "exceedingly intimate at British headquarters." Corke wrote intelligence reports to Tallmadge in invisible ink or reported verbally to him. Mahoney states that Washington and Tallmadge considered Corke a valuable recruit for the Culper Ring.

A letter by loyalist soldier Nehemia Marks, uncovered in 2015, identifies brothers Nathaniel and Phillip Roe as supporters of the spy ring, with Nathaniel providing intelligence and Phillip material aid. The letter also provides evidence that the Culper ring operated in Drowned Meadow beyond Setauket and Oyster Bay, as previously believed. The letter is housed in the William L. Clements library at the University of Michigan, where it was discovered by a former resident of Port Jefferson researching the Culper Ring.

Women in the Ring

Women were informants for or participants in the Culper Ring, including Agent 355, whose identity remains unknown; Anna Strong; Robert Townsend's sister Sally Townsend; and Abraham Woodhull's sister Mary Underhill, who provided important information about Major John Andre and his alias of John Anderson, according to some sources.

Twentieth Century disclosure of the Ring

The general public was unaware of the Ring's existence until the 1930s. Robert Townsend's identity as "Culper, Jr." was discovered in 1929, with the examination of old letters written by Townsend in the Townsend family home. Historian Morton Pennypacker reviewed the letters and noticed that the handwriting in letters from the trunk, written by Robert Townsend, was similar to handwriting in letters written by "Samuel Culper, Jr." in George Washington's collection. Other evidence later corroborated Townsend's identity. James Rivington was confirmed by scholars to be a member of the ring only in the 1950s.

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